Hydrochloric Acid → (R)-(R)-quinuclidin-3-yl 2-amino-2-phenylacetate bis hydrochloride

HRID 1529525Notes

Reaction equation

HRID 1529525 reaction equation
C(OC([NH:8][C@H:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:27].C(OCC)C>O1CCOCC1>[ClH:27].[ClH:27].[NH2:8][C@H:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]2)[CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67607970(R)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86720688(R)-(R)-quinuclidin-3-yl 2-amino-2-phenylacetate bis hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)—(R)-quinuclidin-3-yl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate (0.608 g, 1.687 mmol) in anhydrous dioxane (6 mL) was added 2M HCl in diethyl ether (5.2 mL, 10.4 mmol). The reaction mixture was stirred at room temperature for 20 hours. The solvent was removed in vacuo to afford the title compound as a white solid (0.564 g, quantitative yield).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-33d1de9311374424b04609f85cdfdde8
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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